Find Hotels with Free Wifi in Chestertown, MD

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Our top choices for Chestertown hotels with free wifi

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (859)
"Everything was well!"
United States
Ahmed
$102 nightly
The price is $113
Dec 21 - Dec 22
Total with taxes and fees
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
$72 nightly
The price is $80
Dec 20 - Dec 21
Total with taxes and fees
Red Roof Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 15 - Dec 16
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
$64 nightly
The price is $70
Dec 24 - Dec 25
Total with taxes and fees
Driftwood Inn

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (649)
"The room was great and the staff was even better!"
United States
STEVEN
$93 nightly
The price is $103
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (601)
"very pet friendly!!"
United States
larry
$90 nightly
The price is $101
Dec 20 - Dec 21
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (320)
"The room was spotless, courteous staff, and a wonderful breakfast to start my day "
United States
Alan
$108 nightly
The price is $120
Dec 21 - Dec 22
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
$93 nightly
The price is $103
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
"Everything was great"
United States
Diane
$68 nightly
The price is $75
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn Smyrna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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